Benzyl isocyanate → HCID 178509306, compound

HRID 82738Notes

Reaction equation

HRID 82738 reaction equation
[NH2:1][C:2]1[C:3]([C:7](=[N:17][OH:18])[NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([Cl:16])[CH:10]=2)=[N:4][O:5][N:6]=1.C(N(CC)C(C)C)(C)C.[CH2:28]([N:35]=[C:36]=[O:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>ClCCl>[NH2:1][C:2]1[C:3]([C:7](=[N:17][O:18][C:36]([NH:35][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:37])[NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([Cl:16])[CH:10]=2)=[N:4][O:5][N:6]=1

Participants

5

Reactant 3

HCID 76639Benzyl isocyanateHCID 81531DiisopropylethylamineHCID 178509312HCID 178509312, compound

Product 1

HCID 178509306HCID 178509306, compoundYield 24.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-amino-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide (50 mg, 0.18 mmol) and N,N-diisopropylethylamine (64 μL, 0.37 mmol) in dichloromethane (2 mL) was treated with benzyl isocyanate (29 mg, 0.22 mmol) and stirred for 3 h. The reaction mixture was concentrated and purified by preparative LCMS to give the desired product (18 mg, 24%). LCMS for C17H15ClFN6O3 (M+H)+: m/z=405.0.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-1503e17e19da41749d9878e6008bf082
Source dataset
uspto-grants-2014_09
Patent number
US08846726B2

Reaction notes

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